Regioselective syntheses of 5-polyfluoroalkyl-3-hydroxyfuranes by oxidative cyclization of 6-polyfluoroalkyl-1-arylhexane-1,3,5-triones with hypervalent iodine(III) compounds

IF 1.6 4区化学 Q3 CHEMISTRY, INORGANIC & NUCLEAR

Journal of Fluorine Chemistry Pub Date : 2026-02-01 Epub Date: 2026-02-02 DOI:10.1016/j.jfluchem.2026.110542

Ivan A. Kochnev, Alexey Y. Barkov

引用次数: 0

Abstract

In this work, regioselective cyclization of 6-polyfluoroalkyl-1-arylhexane-1,3,5-triones to 5-polyfluoroalkyl-3-hydroxyfuranes is reported. The synthesis of 5-polyfluoroalkyl-3-hydroxyfuranes is based on hypervalent iodine (III)-mediated oxidative cyclization of 6-polyfluoroalkyl-1-arylhexane-1,3,5-triones in DCM. The effect of the hypervalent iodine (III) reagents, bases and solvents has been studied. This convenient and simple method allows the gram-scale synthesis of 5-polyfluoroalkyl-3-hydroxyfuranes with yields up to 67 %.

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6-多氟烷基-1-芳基己烷-1,3,5-三酮与高价碘（III）化合物氧化环化合成5-多氟烷基-3-羟基呋喃

本文报道了6-多氟烷基-1-芳基己烷-1,3,5-三酮的区域选择性环化成5-多氟烷基-3-羟基呋喃。基于高价碘（III）介导的DCM中6-多氟烷基-1-芳基己烷-1,3,5-三酮的氧化环化，合成了5-多氟烷基-3-羟基呋喃。研究了高价碘（III）的试剂、碱和溶剂的影响。该方法简便、简单，可实现克级5-多氟烷基-3-羟基呋喃的合成，收率可达67%。

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来源期刊

Journal of Fluorine Chemistry 化学-无机化学与核化学

CiteScore

3.80

自引率

10.50%

发文量

审稿时长

33 days

期刊介绍： The Journal of Fluorine Chemistry contains reviews, original papers and short communications. The journal covers all aspects of pure and applied research on the chemistry as well as on the applications of fluorine, and of compounds or materials where fluorine exercises significant effects. This can include all chemistry research areas (inorganic, organic, organometallic, macromolecular and physical chemistry) but also includes papers on biological/biochemical related aspects of Fluorine chemistry as well as medicinal, agrochemical and pharmacological research. The Journal of Fluorine Chemistry also publishes environmental and industrial papers dealing with aspects of Fluorine chemistry on energy and material sciences. Preparative and physico-chemical investigations as well as theoretical, structural and mechanistic aspects are covered. The Journal, however, does not accept work of purely routine nature. For reviews and special issues on particular topics of fluorine chemistry or from selected symposia, please contact the Regional Editors for further details.